Real Estate Investment Properties for Sale in Longwood, FL
Looking for investment property in Longwood, FL with high ROI ?
Explore a variety of short-term homes & houses in Longwood, FL. Invest wisely with VRBO & Longwood, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Longwood, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
3996 RADLEY COURT #3996Longwood, FLOne or more photo(s) has been virtually staged. Do not miss this excellent opportunity to ... |
2 beds | 2 baths | 1,427 sq.ft. |
$245,000 |
Airbnb cash on cash: -1.7%
|
4102 CLUBSIDE DRIVE #4102Longwood, FLSpacious 2-Bedroom Corner Unit in Clubside at Sabal Point â Private, Updated & Move-In R... |
2 beds | 3 baths | 1,380 sq.ft. |
$222,000 |
Airbnb cash on cash: -1.38%
|
1665 GRANGE CIRCLELongwood, FLExpect to be impressed with this beautiful 3-bedroom, 2-bathroom home featuring stunning u... |
3 beds | 2 baths | 2,189 sq.ft. |
$415,000 |
Airbnb cash on cash: 4.08%
|
899 LORMANN CIRCLELongwood, FLWelcome to your Longwood retreat. Enjoy the peace of mind that comes with no HOA! This me... |
3 beds | 2 baths | 969 sq.ft. |
$299,490 |
Airbnb cash on cash: 7.12%
|
2681 AZALEA DRIVELongwood, FLWelcome to your springtime retreat in the desirable Lake Brantley area! Nestled on a gener... |
3 beds | 2 baths | 1,399 sq.ft. |
$345,000 |
Airbnb cash on cash: 5.28%
|
102 N SILVER CLUSTER COURTLongwood, FLWelcome to 102 Silver Cluster Ct N in Longwood, a beautifully maintained pool home under $... |
3 beds | 2 baths | 1,166 sq.ft. |
$395,000 |
Airbnb cash on cash: 4.46%
|
1870 CROWLEY CIRCLE ELongwood, FLShort Sale. Welcome to your peacefull oasis located on a full acre. Spacious floor plan wi... |
4 beds | 4 baths | 3,258 sq.ft. |
$625,000 |
Airbnb cash on cash: 4.76%
|
561 SHINING ARMOR LANELongwood, FLInvest with success and buy through Auction.com. This bank-owned investment property is a ... |
N/A beds | N/A baths | N/A |
$358,000 |
Airbnb cash on cash: 2.29%
|
2522 THICKET RIDGE COURTLongwood, FLUnder contract-accepting backup offers. One or more photo(s) was virtually staged. Low-m... |
3 beds | 2 baths | 1,842 sq.ft. |
$399,000 |
Airbnb cash on cash: 4.46%
|
884 CUTLER ROADLongwood, FLOne or more photo(s) has been virtually staged. Welcome to this beautifully updated 5-bedr... |
5 beds | 3 baths | 2,601 sq.ft. |
$639,000 |
Airbnb cash on cash: N/A
|
202 CROWN OAKS WAY #201Longwood, FLDiscover this spacious 2-bedroom, 2-bathroom second-floor condo located in the highly desi... |
2 beds | 2 baths | 1,119 sq.ft. |
$139,900 |
Airbnb cash on cash: 2.63%
|
105 DURHAM PLACE #105Longwood, FLDiscover 105 Durham Place, a 2-bedroom, 2-bathroom condo in the sought-after Wekiva commun... |
2 beds | 2 baths | 1,427 sq.ft. |
$260,000 |
Airbnb cash on cash: -1.66%
|
413 WILLOWBROOK LANELongwood, FLWelcome home to this spacious 4-bedroom, 2-bath pool residence with dedicated office, nest... |
4 beds | 2 baths | 2,740 sq.ft. |
$582,999 |
Airbnb cash on cash: 5.91%
|
114 JUNIPER LANELongwood, FLOne or more photo(s) has been virtually staged. Quality that speaks for itself. Pride of o... |
2 beds | 2 baths | 2,049 sq.ft. |
$460,000 |
Airbnb cash on cash: -0.39%
|
308 SMOKERISE BOULEVARDLongwood, FLWelcome to 308 Smokerise Blvd., tucked away on a quiet corner lot within a cul-de-sac in t... |
4 beds | 2 baths | 2,352 sq.ft. |
$650,000 |
Airbnb cash on cash: 4.87%
|
255 E HORNBEAM DRIVELongwood, FLWelcome to this exquisitely remodeled residence in the highly desirable community of Sabal... |
4 beds | 3 baths | 2,309 sq.ft. |
$632,000 |
Airbnb cash on cash: 4.95%
|
257 GARY BOULEVARDLongwood, FLUnder contract-accepting backup offers. Three bedrooms, two baths, a pool, and no HOA in o... |
3 beds | 2 baths | 1,267 sq.ft. |
$375,000 |
Airbnb cash on cash: 5.04%
|
385 BRASSIE DRIVELongwood, FLUnder contract-accepting backup offers. Once in a life time opportunity to own this amazin... |
4 beds | 4 baths | 3,412 sq.ft. |
$660,000 |
Airbnb cash on cash: 4.79%
|
451 STANTON PLACELongwood, FLWelcome to Governorâs Point, a highly sought-after community in Wekiva, located in Longw... |
3 beds | 3 baths | 1,682 sq.ft. |
$334,900 |
Airbnb cash on cash: 3.82%
|
860 Charlotte St.Longwood, FL4-Bed / 3.5-Bath Home Built in 2006. -needs updating, new ac. |
4 beds | 4 baths | N/A |
$449,000 |
Airbnb cash on cash: 7.55%
|
1025 BUCKSAW PLACELongwood, FLShort Sale. Short Sale â Opportunity awaits! This home has been winterized and is ready ... |
3 beds | 3 baths | 2,289 sq.ft. |
$419,000 |
Airbnb cash on cash: 3.4%
|
105 KILKENNY COURTLongwood, FLWelcome to 105 Kilkenny Ct and this beautifully updated Wekiva home nestled on a quiet cul... |
3 beds | 2 baths | 1,562 sq.ft. |
$435,000 |
Airbnb cash on cash: 3.91%
|
1386 S RIDGE LAKE CIRCLELongwood, FLUnder contract-accepting backup offers. *** MULTIPLE OFFERS **** RARE FIND in the sought o... |
4 beds | 2 baths | 2,263 sq.ft. |
$535,000 |
Airbnb cash on cash: 6.23%
|
126 SANDALWOOD WAYLongwood, FLUnder contract-accepting backup offers. **This house comes with a REDUCED RATE through the... |
3 beds | 2 baths | 1,354 sq.ft. |
$404,900 |
Airbnb cash on cash: 4.06%
|
150 ESSEX DRIVELongwood, FLUnder contract-accepting backup offers. Step into the warmth and charm of this rare cabin-... |
3 beds | 2 baths | 1,449 sq.ft. |
$432,000 |
Airbnb cash on cash: 3.89%
|
1742 FIFESHIRE COURTLongwood, FLWelcome home to your own immaculate sparkling screened in pool home nestled in a cul-de-sa... |
5 beds | 7 baths | 4,053 sq.ft. |
$1,275,000 |
Airbnb cash on cash: N/A
|
305 SWEETWATER CLUB CIRCLELongwood, FLLocated behind the gates of the exclusive, guard-gated Sweetwater Club Tennis Community, t... |
4 beds | 6 baths | 4,975 sq.ft. |
$1,400,000 |
Airbnb cash on cash: 1.35%
|
2010 E TRIANGLE DRIVELongwood, FLUnder contract-accepting backup offers. IMPORTANT NOTE: Current Flood insurance policy and... |
3 beds | 2 baths | 1,684 sq.ft. |
$339,800 |
Airbnb cash on cash: 5.54%
|
1319 SUMMERTREE COURTLongwood, FLWelcome to 1319 Summertree Ct, one of the larger homes in the highly desirable Bay Lagoon ... |
3 beds | 3 baths | 2,133 sq.ft. |
$499,999 |
Airbnb cash on cash: 3.13%
|
572 LAKE WILDMERE COVELongwood, FLHere is your opportunity to own a true Turn Key Investment property.This almost new townho... |
4 beds | 5 baths | 2,294 sq.ft. |
$455,000 |
Airbnb cash on cash: 6.54%
|
486 N PIN OAK PLACE #112Longwood, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. **... |
2 beds | 1 baths | 959 sq.ft. |
$187,900 |
Airbnb cash on cash: 1.44%
|
410 GEORGIA AVENUELongwood, FLUnder contract-accepting backup offers. This fully renovated home blends style and functio... |
3 beds | 2 baths | 1,588 sq.ft. |
$435,000 |
Airbnb cash on cash: 3.88%
|
450 LONGMEADOW LANELongwood, FLExcellent opportunity in Sabal Point. POOL house with two NEW HVACs. 4 bedrooms, 3.5 bathr... |
4 beds | 4 baths | 2,623 sq.ft. |
$559,000 |
Airbnb cash on cash: 6.27%
|
1310 RIDGE ROADLongwood, FLWelcome to your own private oasis in the highly desirable Longwood area! This beautifully ... |
3 beds | 2 baths | 1,520 sq.ft. |
$485,000 |
Airbnb cash on cash: 3.37%
|
803 SWEETWATER CLUB BOULEVARDLongwood, FLOne or more photo(s) has been virtually staged. In the heart of the coveted, gated Sweetwa... |
4 beds | 6 baths | 5,344 sq.ft. |
$1,575,000 |
Airbnb cash on cash: 0.72%
|
322 N SHADOWBAY BOULEVARDLongwood, FLWelcome to Lake Vista at Shadowbay - No HOA and No Restrictions! This beautiful and well-m... |
3 beds | 2 baths | 1,599 sq.ft. |
$499,900 |
Airbnb cash on cash: 3.68%
|
112 DES PINAR LANELongwood, FLUnder contract-accepting backup offers. Fully Remodeled Luxury Pool Home | No HOA | Priced... |
4 beds | 2 baths | 1,604 sq.ft. |
$419,000 |
Airbnb cash on cash: 8.65%
|
307 COBLE DRIVELongwood, FLSome homes just feel right the moment you walk in⦠and 307 Coble Drive is one of them. ... |
4 beds | 2 baths | 1,987 sq.ft. |
$475,000 |
Airbnb cash on cash: 7.19%
|
116 WILD HOLLY LANELongwood, FLShort Sale. This townhome offers incredible potential, featuring a versatile separate offi... |
2 beds | 2 baths | 1,722 sq.ft. |
$245,000 |
Airbnb cash on cash: 0.65%
|
183 PARSONS ROADLongwood, FLEscape into peace, nature and privacy on 12.3 acres of delightful Old Florida property. Wa... |
4 beds | 3 baths | 3,731 sq.ft. |
$5,800,000 |
Airbnb cash on cash: -0.49%
|
Real Estate investment in Longwood, FL
There are 139 properties for sale in the city of Longwood . The median list price in Longwood is $435,000 and the average price per square foot is $206. In April 2026, the average monthly cash on cash return in Longwood is 4.00%. The average monthly rental income in Longwood is $2,498.